@article{9c1e2ac1cf99425f91c7ec2cfdc0e94e,
title = "Crystals of Benzamide, the First Polymorphous Molecular Compound, Are Helicoidal",
abstract = "The growth of spontaneously twisted crystals is a common but poorly understood phenomenon. An analysis of the formation of twisted crystals of a metastable benzamide polymorph (form II) crystallizing from highly supersaturated aqueous and ethanol solutions is given here. Benzamide, the first polymorphic molecular crystal reported (1832), would have been the first helicoidal crystal observed had the original authors undertaken an analysis by light microscopy. Polymorphism and twisting frequently concur as they are both associated with high thermodynamic driving forces for crystallization. Optical and electron microscopies as well as electron and powder X-ray diffraction reveal a complex lamellar structure of benzamide form II needle-like crystals. The internal stress produced by the overgrowth of lamellae is shown to be able to create a twist moment that is responsible for the observed non-classical morphologies.",
keywords = "benzamide, disorder, internal stress, polymorphism, twisted crystals",
author = "Shtukenberg, {Alexander G.} and Ran Drori and Sturm, {Elena V.} and Netta Vidavsky and Asaf Haddad and Jason Zheng and Estroff, {Lara A.} and Haim Weissman and Wolf, {Sharon G.} and Eyal Shimoni and Chao Li and Noalle Fellah and Efi Efrati and Bart Kahr",
note = "Funding Information: This work was primarily supported by the New York University Materials Research Science and Engineering Center (MRSEC) program of the National Science Foundation under award number DMR‐1420073. Funding support was also provided by the National Science Foundation (DMR‐1608374, with a supplement through the United States–Israel Binational Science Foundation, DMR‐BSF 2015670). Use of the Advanced Photon Source at Argonne National Laboratory was supported by the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences, under Contract No. DE‐AC02‐06CH11357. This work made use of the Cornell Center for Materials Research Shared Facilities which are supported through the NSF MRSEC program (grant DMR‐1719875). We are grateful to Dr. Lynn W. Ribaud and Dr. Saul D. Lapidus for providing assistance in collecting synchrotron powder diffraction data at Advanced Photon Source. We acknowledge Dr. Chunhua Hu (NYU Department of Chemistry X‐ray Diffraction Facility) and the NSF Chemistry Research Instrumentation and Facilities Program (CHE‐0840277) for the powder microdiffractometer. We also thank Dr. A. Kasper for performing lyophilization of benzamide. Funding Information: This work was primarily supported by the New York University Materials Research Science and Engineering Center (MRSEC) program of the National Science Foundation under award number DMR-1420073. Funding support was also provided by the National Science Foundation (DMR-1608374, with a supplement through the United States–Israel Binational Science Foundation, DMR-BSF 2015670). Use of the Advanced Photon Source at Argonne National Laboratory was supported by the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences, under Contract No. DE-AC02-06CH11357. This work made use of the Cornell Center for Materials Research Shared Facilities which are supported through the NSF MRSEC program (grant DMR-1719875). We are grateful to Dr. Lynn W. Ribaud and Dr. Saul D. Lapidus for providing assistance in collecting synchrotron powder diffraction data at Advanced Photon Source. We acknowledge Dr. Chunhua Hu (NYU Department of Chemistry X-ray Diffraction Facility) and the NSF Chemistry Research Instrumentation and Facilities Program (CHE-0840277) for the powder microdiffractometer. We also thank Dr. A. Kasper for performing lyophilization of benzamide. Publisher Copyright: {\textcopyright} 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",
year = "2020",
month = aug,
day = "17",
doi = "10.1002/anie.202005738",
language = "English (US)",
volume = "59",
pages = "14593--14601",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "34",
}